US EPA

8408215 

Journal Article 

LIQUID-PHASE OXIDATION OF o-NITROTOLUENE BY NITRIC ACID 

Sushchev, VG; Dolmatov, VY; Aleksenskii, AE; V'Yunov, KA 

1987 

Yes 

Journal of Applied Chemistry of the USSR
ISSN: 0021-888X 

60 

5 pt 1 

1022-1026 

English 

The kinetics of oxidation of o-nitrotoluene were investigated and methods of optimizing the process, directed toward increasing the yield of o-nitrobenzoic acid and decreasing the concentration of picric acid in the products of the reaction, were sought in the present study. The mechanism of oxidation of the methyl group in o-nitrotoluene includes elimination of the hydrogen atom in the methyl group under the effect of free radicals, and this stage apparently limits the rate of the entire process. The results obtained indicate that o-nitrobenzoic and picric acid are formed in both cases, and the rate of these reactions is much higher than the rate of oxidation of o-nitrotoluene. The anomalous character of oxidation of o-nitrotoluene in comparison to o-, m-, p-chloro- and m-p-nitrotoluenes is due to the additional reaction of the nitro group with the partially oxidized methyl fragment.